EP-A-44,209 discloses herbicidal sulfonamides of formula ##STR1## wherein R is H, F, Cl, Br, NO.sub.2, CF.sub.3, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy;
R.sub.1 is H, Cl or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.2 is H or CH.sub.3 ; and PA1 L is, among other values, CO.sub.2 R.sub.10, CONR.sub.3 R.sub.4, CN, Cl, Br, NR.sub.3 R.sub.4, S(O).sub.n R.sub.7, SO.sub.2 NR.sub.3 R.sub.4 and OR.sub.9. PA1 R.sub.9 and R.sub.10 are, among other values, H or CH.sub.3 ; and PA1 R.sub.11 is COR.sub.24 or a C.sub.1 -C.sub.4 alkyl group substituted with, among other values, CN, NO.sub.2, OH, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkoxy, NR.sub.12 R.sub.13 and SO.sub.2 NR.sub.15 R.sub.16. PA1 R.sub.1 is C.sub.1 -C.sub.3 alkyl; and PA1 R.sub.2 is C.sub.2 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyloxy, C.sub.3 -C.sub.6 alkenylthio, C.sub.3 -C.sub.6 alkynylthio, OCH.sub.2 CH.sub.2 OCH.sub.3, OCH.sub.2 CH.sub.2 SCH.sub.3, CH.sub.2 F, CHF.sub.2, OCF.sub.2 H, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, OCH.sub.2 CH.sub.2 Cl, C.sub.2 -C.sub.6 alkyl substituted with 1-3 atoms of F or Cl or C.sub.1 -C.sub.4 alkyl substituted with C.sub.1 -C.sub.2 alkoxy or C.sub.1 -C.sub.2 alkylthio; PA1 A is alkynyl, alkyl which is unsubstituted or substituted by halogen, alkoxy, alkylthio, alkylsylfinyl, alkylsulfonyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl, or alkenyl which is unsubstituted or substituted by the substituents given above for alkyl, or A is a phenyl or benzyl group; PA1 E is methine; PA1 X is oxygen, sulfur, or a sulfinyl or sulfonyl bridge; PA1 Z is oxygen or sulfur; PA1 R.sub.1 is hydrogen, alkyl or alkoxy; PA1 R.sub.2 is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, amino, alkylamino, di-alkylamino, cycloalkyl or alkoxyalkyl, R.sub.3 is hydrogen, halogen, alkyl, alkenyl, haloalkyl, --CO--NR.sub.8 R.sub.9, --CN, --COR.sub.10, --NR.sub.1 R.sub.7 or --NR.sub.1 --COR.sub.12 ; PA1 R.sub.4 is hydrogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, halogen, or alkoxyalkyl; PA1 R.sub.5 is independently selected from the same groups as R.sub.3 or --X--R.sub.6 ; PA1 R.sub.6 and R.sub.7 are each alkyl, alkenyl or alkynyl; PA1 R.sub.8 and R.sub.9 independently of one another are each hydrogen, alkyl, alkenyl or alkynyl; PA1 R.sub.10 is hydrogen, alkyl or haloalkyl; PA1 R.sub.11 is hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, phenyl or benzyl; and PA1 R.sub.12 is the same as R.sub.1 but independent thereof. PA1 R.sub.3 and R.sub.4 independently of one another denote hydrogen or (C.sub.1 -C.sub.4)-alkyl; PA1 R.sub.5 denotes hydrogen, halogen, (C.sub.1 -C.sub.4)-alkylamino, di(C.sub.1 -C.sub.4)-alkylamino, (C.sub.1 -C.sub.4)-alkyl which is optionally monosubstituted or poly-substituted by halogen, (C.sub.1 -C.sub.3)-alkoxy or (C.sub.1 -C.sub.3)-alkylthio, or denotes (C.sub.1 --C.sub.4)-alkoxy, (C.sub.1 -C.sub.4)-alkylthio, allyloxy or propargyloxy; PA1 R.sub.6 and R.sup.7 independently of one another denote hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-halogenoalkyl, halogen or (C.sub.1 -C.sub.2)-alkoxy-(C.sub.1 -C.sub.2)-alkyl; PA1 R.sub.8 denotes (C.sub.1 -C.sub.4)-alkyl, (C.sub.2 -C.sub.4)-alkenyl or benzyl; PA1 R.sub.9 denotes (C.sub.1 -C.sub.4)-alkyl which is optionally substituted by CN or (C.sub.1 -C.sub.4)-alkoxycarbonyl, or denotes (C.sub.1 -C.sub.4)-alkoxy; PA1 m denotes the number 1 to 3; PA1 n denotes th number 0 to 2; and PA1 X denotes a methine group or nitrogen. PA1 W is O or S; PA1 R is H or CH.sub.3 ; PA1 R.sub.1 is F, Cl, Br, NO.sub.2, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 haloalkenyl, C.sub.2 -C.sub.4 alkynyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, OCH.sub.2 CH.sub.2 OCH.sub.3, C.sub.1 -C.sub.4 haloalkoxy, C.sub.3 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.4 haloalkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, CO.sub.2 R.sub.3, CONR.sub.4 R.sub.5, SO.sub.2 NR.sub.4 R.sub.5, SO.sub.2 N(OCH.sub.3)CH.sub.3, S(O).sub.n R.sub.6, OSO.sub.2 R.sub.7, C.sub.1 -C.sub.2 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, OH or C.sub.1 -C.sub.2 alkylthio, CH.sub.2 CN, C.sub.6 H.sub.5, ##STR9## PA1 R.sub.4 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.5 is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.4 and R.sub.5 may be taken together to form (CH.sub.2).sub.3 or (CH.sub.2).sub.4 ; PA1 R.sub.6 is C.sub.1 -C.sub.3 alkyl, CH.sub.2 CH.dbd.CH.sub.2 or CH.sub.2 C.tbd.CH; PA1 R.sub.7 is C.sub.1 -C.sub.3 alkyl or N(CH.sub.3).sub.2 ; PA1 R.sub.8 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, CH.sub.2 CH.sub.2 Cl, CH.sub.2 CH.sub.2 F, C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 or SCH.sub.3 or C.sub.3 -C.sub.6 cycloalkyl; PA1 R.sub.9 is C.sub.1 -C.sub.2 alkyl; PA1 R.sub.10 and R.sub.11 are independently C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, NHCH.sub.3 or N(CH.sub.3).sub.2 ; PA1 R.sub.12 and R.sub.13 are independently H or C.sub.1 -C.sub.2 alkyl; PA1 R.sub.14 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.15 is H or CH.sub.3 ; PA1 R.sub.16 is H, C.sub.1 -C.sub.2 alkyl or F; PA1 R.sub.17 is H or C.sub.1 -C.sub.2 alkyl; PA1 R.sub.18 is C.sub.1 -C.sub.2 alkyl; PA1 R.sub.19 is H, Si(CH.sub.3).sub.3 or C.sub.1 -C.sub.2 alkyl; PA1 R.sub.20 is H or C.sub.1 -C.sub.2 alkyl; PA1 p is 1 or 2; PA1 n is 0, 1, or 2; PA1 A is ##STR12## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino; PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkynyl, C.sub.3 -C.sub.5 cycloalkyl, azido, cyano, ##STR13## or N(OCH.sub.3)CH.sub.3 ; m is 2 or 3; PA1 Q.sub.1 and Q.sub.2 are independently O or S; PA1 R.sub.a is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.b and R.sub.c are independently C.sub.1 -C.sub.3 alkyl; PA1 Z is CH, N, CCH.sub.3, CC.sub.2 H.sub.5, CCl or CBr; PA1 Y.sub.1 is O or CH.sub.2 ; PA1 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA1 X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ; PA1 Y.sub.2 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, SC.sub.2 H.sub.5, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA1 Y.sub.3 is H or CH.sub.3 ; PA1 X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl; PA1 Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl; PA1 (1) when X is halogen, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, OCF.sub.2 H or N(OCH.sub.3)CH.sub.3 ; PA1 (2) when X or Y is C.sub.1 haloalkoxy, then Z is CH; PA1 (3) when W is S, then R is H, A is A-1, Z is CH or N, and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or ##STR14## (4) when the total number of carbon atoms of X and Y is greater than four, then the combined number of carbons of R.sub.1 and R.sub.2 is less than or equal to six; PA1 (5) when R.sub.2 is C(O)R.sub.17, then R.sub.1 is other than C.sub.1 -C.sub.4 haloalkyl or C.sub.2 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, OH or C.sub.1 -C.sub.2 alkylthio, and Y is other than cyclopropyl; PA1 (6) when Y is C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.2 -C.sub.5 alkylsulfinylalkyl or C.sub.2 -C.sub.5 alkylsulfonylalkyl, then R.sub.2 is other than CH(R.sub.17)NO.sub.2 ; PA1 (7) X.sub.4 and Y.sub.4 are not simultaneously Cl; and PA1 (8) when R.sub.2 is C(O)R.sub.17 then R.sub.1 is other than SO.sub.2 NR.sub.4 R.sub.5 and SO.sub.2 N(OCH.sub.3)CH.sub.3. PA1 1. Compounds of Formula I where PA1 2. Compounds of Prefererd 1 where PA1 3. Compounds of Preferred 2 where PA1 6. Compounds of Preferred 5 where PA1 7. Compounds of Preferred 6 where R.sub.1 is F, Cl, Br, NO.sub.2, CH.sub.3, CF.sub.3 C.sub.1 -C.sub.2 alkoxy, allyloxy, OC(Cl).dbd.CHCl, CO.sub.2 CH.sub.3, CO.sub.2 C.sub.2 H.sub.5, CO.sub.2 NHCH.sub.3, CO.sub.2 N(CH.sub.3).sub.2, SO.sub.2 NHCH.sub.3 SO.sub.2 N(CH.sub.3).sub.2, SO.sub.2 CH.sub.3, SO.sub.2 C.sub.2 H.sub.5, OSO.sub.2 CH.sub.3, OSO.sub.2 C.sub.2 H.sub.5, R.sub.1 --A, R.sub.1 --B or R.sub.1 --C. PA1 U.S. Pat. No. 4,398,939 (issued 8/16/83) teaches the formation of n-butylsulfonylureas from sulfonamides followed by phosgenation to give the sulfonyl isocyanates. Alternatively, the sulfonamides can be treated with thionyl chloride followed by phosgenation to afford the sulfonyl isocyanates. Additionally, methylcarbamate derivatives of compounds of Formula III react with sulfonamides in the presence of trimethylaluminum to give sulfonylureas. PA1 U.S. Pat. No. 4,443,245 (issued 4/17/84) teaches two methods for the synthesis of sulfonylureas. Either a phenyl carbamate of a sulfonamide and a heterocyclic amine, or a sulfonamide and a phenyl carbamate of a heterocyclic amine couple to give a sulfonylurea in an inert solvent with base. PA1 Aromatic nitro groups may be transformed into sulfonyl chlorides by reduction, diazotization and coupling with sulfur dioxide/cupric chloride as taught in U.S. Pat. No. 4,310,346 (issued 1/12/82). PA1 European Publication No. 94,821 (published 11/23/83) describes the displacement of aromatic halides with thiolate anions and subsequent oxidative chlorination to yield sulfonyl chlorides. PA1 Halogen-metal exchange of aromatic halides or proton-metal exchange of aromatics followed by quenching with sulfur dioxide gives sulfinate salts. These salts yield sulfonyl chlorides upon reaction with N-chlorosuccinimide as taught in U.S. Pat. No. 4,481,029 (issued 11/6/84). Directed proton-metal exchange of aromatic compounds has been reviewed by Gschwend and Rodriguez, Org. Reactions, 26 (1979), 1. Directed lithiation of aryl-N-t-butylsulfonamides is described by J. G. Lombardino, J. Org. Chem., 36 (1971), 1843. Also, aryllithiums may be converted directly to arylsulfonyl chlorides with sulfuryl chloride as described in S. N. Bhattacharya, et. al., J. Chem. Soc. C, (1968), 1265. PA1 Electrophilic chlorsulfonation of an aromatic ring to give a sulfonyl chloride is well known in the literature. This technique works best for alkyl aryl ethers and alkyl aromatics. Its application is described by E. H. Huntress and F. H. Carten, J. Am. Chem. Soc., 62 (1940), 511-14 and 603-4. PA1 Transformation of phenols of sulfonyl chlorides can be accomplished by the formation of a thiocarbamate, rearrangement, hydrolysis and oxidative chlorination as described by M. S. Newman and H. A. Kames, J. Org. Chem., 31 (1966), 3980. PA1 Nitriles can be prepared by nucleophilic displacement of benzyl halides, usually benzyl chlorides or bromides, with potassium or sodium cyanide. Many solvents are applicable, but frequently dimethylsulfoxide is used. Thus, a benzyl bromide of formula IV can be contacted with potassium cyanide in dimethylsulfoxide for 0.5 h to 24 h at 20.degree. to 140.degree. C. For a review of this reaction, refer to Friedrich and Wallenfels, in Rappoport. "The Chemistry of the Cyano Group", pp. 77-86, Interscience Publishers, New York, 1970. PA1 Heavy metal cyanides and benzylhalides react to give isonitriles. The reaction is best carried out in the dark using silver cyanide and a benzyl iodide. Typical procedures are given by A. Gautier, Ann. Chem., 142 (1867), 28 and H. L. Jackson and B. C. McKusick, Org. Syn., Col. Vol. IV, 438. PA1 Compounds of Formula II may be prepared by reacting an azide anion with a benzyl halide. Typically sodium azide in alcohol or wet acetone is mixed with a benzyl bromide at 20.degree.-100.degree. C. This nucleophilic displacement is reviewed in Biffin, Miller and Paul, in Patai, "The Chemistry of the Azido Group," pp. 57-119, Interscience Pub., New York, 1971. PA1 Alkyl phosphites are heated with benzylic halides to give phosphonates. The reaction is known as the Arbuzov reaction and it is reviewed by Arbuzov, Pure Appl. Chem., 9 (1964), 307-335. PA1 Tertiary amines are prepared by alkylation of a secondary amine with a benzylic halide. The reaction is well documented in the literature. PA1 Primary amines can be prepared by reduction of compounds of Formula II where R.sub.2 is azide. Generally lithium aluminum hydride or hydrogen and palladium catalyst are used. PA1 Alkali alkylselenides can be prepared by in situ combination of an alkali metal t-butoxide with the selenol HSeR.sub.14 in the solvent to be used for the displacement reaction. The selenols, HSeR.sub.14, can be prepared by a variety of methods reviewed by D. L. Klayman, "Selenols and their Derivatives" in Organic Selenium Compounds: Their Chemistry and Biology, D. L. Klayman, W. H. H. Gunther ed., New York, 1973, and K. J. Irgolic and M. V. Kudchadker, "Organic Chemistry of Selenium" in Selenium, R. A. Zingaro, W. C. Copper ed., Van Nostrand Reinhold, New York, 1974. PA1 Treatment of alkyl benzene derivatives with N-chlorosuccinimide, NCS, in a suitable solvent, such as carbon tetrachloride or dichloromethane, and catalyzed by light or a free radical initiator, such as azoisobutyronitrile or benzoyl peroxide, gives the benzylic chloride. PA1 Treatment of a benzylic alcohol with thionyl chloride, either neat or in the presence of a base such as pyridine, gives the benzylic chloride. For typical examples, see H. Gilman and J. E. Kirby, J. Am. Chem. Soc., 51, 3475 (1929) and M. S. Newman, J. Am. Chem. Soc., 62, 2295 (1940). PA1 Treatment of alkyl benzene derivatives with N-bromosuccinimide by a method analogous to the case of N-chlorosuccinimide gives the benzylic bromide. Benzylic alcohol in an inert solvent such as benzene of dichloromethane react with phosphorus tribromide to give benzylic bromides. PA1 Treatment of a benzylic chloride or benzylic bromide with sodium iodide gives the benzylic iodide. The reaction, known as the Finkelstein reaction, works well in refluxing acetone. PA1 Benzylic alcohols may be treated with iodine and phosphorus (red) or phosphorus (red) and phosphorus (yellow) to give the benzylic iodide.
EP-A-112,803 discloses, in part, herbicidal sulfonamides of formula ##STR2##
South African Patent Application 84/2722 discloses herbicidal sulfonamides of formula ##STR3## wherein A is CR.sub.6 R.sub.7 XR.sub.8, CR.sub.9 R.sub.10 R.sub.11 or CHR.sub.7 SCQR.sub.21 ;
EP-A-162,723 discloses 2,5-substituted herbicidal sulfonamides of formula ##STR4## wherein R is H or CH;
U.S. Pat. No. 4,310,346 discloses herbicidal benzenesulfonylureas containing an o-sulfonamide moiety which may contain an optional floating substituent selected from F, Cl, Br, C.sub.1 -C.sub.3 alkyl, NO.sub.2, OCH.sub.3, C(O)R.sub.d, CH.sub.2 OR.sub.d, CF.sub.3, NH.sub.2, NMe.sub.2, CN, CH.sub.2 S(O).sub.n CH.sub.3, S(O).sub.n CH.sub.3, NHC(O)R.sub.d or NHCO.sub.2 R.sub.d ; wherein n is 0, 1 or 2 and R.sub.d is C.sub.1 -C.sub.3 alkyl.
U.S. Pat. No. 4,600,428 discloses N-(cyclopropylpyrimidinyl)-N-aryl-sulfonylyreas of the formula ##STR5## wherein Ar is a phenyl group ##STR6## or a naphthyl group and Q is a group X--A or R.sub.3 ;
South African Patent Application 84/5216 discloses herbicidal sulfonamides of formula ##STR7## in which R.sub.1 and R.sub.2 independently of one another denote hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy or (C.sub.1 -C.sub.4)-alkylthio which are optionally monosubstituted or poly-substituted by halogen, NO.sub.2, (C.sub.1 -C.sub.4)-alkoxycarbonyl, --(C.sub.1 -C.sub.4)--S(O).sub.n --, (C.sub.1 -C.sub.4 -alkyl)--N(R.sub.9 SO.sub.2 --, (C.sub.1 -C.sub.4)-alkenyloxy, (C.sub.1 -C.sub.4)-alkynyloxy, --OSO.sub.2 --(C.sub.1 -C.sub.4)-alkyl, --OSO.sub.2 CF.sub.3, --CONHR.sub.3 or --CON(R.sub.32 ;